As I eventually want to work overseas again, and have done so for the military before... my recommendations:
- Go there as a visitor. For like. A month. Live cheaply, deal with living as much as possible on as little as possible.
If you can do that, living off of nearly nothing and still enjoying your time there more than the comforts of home, then you'll know you're ready to work there. Many cool places to go are expensive to live in--and for a reason. They're cool. So, go there on the month with the crappiest weather, and deal with it.
Don't stay in a nice, fancy hotel/condo, eat out everyday, and vacation, and then come back and say "I want to live there and work there!" Couchsurf, or something like that, and probe into daily life there. It'll give you way more realistic expectations.
I do want to work overseas for the convenience of travel--I want a part-time job where I can go somewhere on my weekends.. but part-time work + time = very little money. You have to know how to survive on it without feeling blue about it to really enjoy your time there.
The other way to do it--get a bad ass job that is viable anywhere and make money no matter where you go. Warning: This is going to cause a lot of nasty school work and networking.
Third way to do it: Intensively practice the other language (if it inspires you) if you're not currently fluent, and become a translator. They have a happy marriage of worlds, but they're paid for their knowledge. If you practice hard, you can learn a language and become more fluent with crappy jobs and earn your way quickly into getting better jobs.